CN104561145A - Preparation method of 1, 3-dioleoyl-2-palmitoyl triglyceride - Google Patents
Preparation method of 1, 3-dioleoyl-2-palmitoyl triglyceride Download PDFInfo
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Abstract
The invention relates to a method for preparing 1, 3-dioleoyl 2-palmitoyl triglyceride by taking palm oil as a raw material. The preparation method comprises the following steps: (1), palm oil is taken as the basic raw material and is hydrolyzed under catalysis of a catalyst so as to prepare an oleic acid and palmitic acid mixture; (2), the oleic acid and palmitic acid mixture is separated; (3), separated palmitic acid is taken as a raw material to synthesize tripalmitin under the action of a catalyst; and (4), lipase catalyzed oleic acid and tripalmitin react to produce 1, 3-dioleoyl-2-palmitoyl triglyceride. The method has the advantages of stable raw material source, low cost, stable and excellent product quality and the like.
Description
Technical field
The present invention relates to a kind of preparation method of organic compound, being specifically related to a kind of take plam oil as the method that OPO prepared by raw material.
Background technology
At present, people's butterfat is the optimum food of generally acknowledged infant.Baby after birth, must absorb the nutritive substance adapted with himself g and D, in order to ensure normal growth and the growth of its health.Natural human milk fat has the constructional feature of oneself uniqueness, the lipid acid (palmitinic acid) that human milk fat is saturated in the middle of the composition of the total fatty acids of triglyceride containing have an appointment 25% massfraction, and be mainly distributed in the mid-way of the glycerol backbone of triglyceride level, i.e. Sn-2 position, its distributive law reaches 65%-70%, to ensure that lipid acid and mineral substance can reach a higher assimilation effect, and provide the energy being about 10% for the growth of infant and normal physiological activity, other some lipid acid, such as oleic acid, linolic acid etc., the most main Sn-1 being distributed in the outside of triglyceride level of these lipid acid, on 3 positions, so the major structural types of triglyceride level in human milk fat is the type of Sn-UStU, what U represented is undersaturated lipid acid, comprise monounsaturated lipid acid and polyunsaturated lipid acid, what St represented is saturated lipid acid, concrete triglyceride level has Sn-OPO, Sn-OPL etc., wherein O representative is oleic acid, what L represented is linolic acid, the constructional feature of these triglyceride level in human milk fat is all digest and assimilate close relationship with infant to fat.
In the fat of vegetables oil and cow's milk, saturated lipid acid is mainly distributed on Sn-1 or the Sn-3 position of the glycerol backbone of triglyceride.In vegetables oil, saturated lipid acid (palmitinic acid) is at the Sn-1 of triglyceride glycerol backbone, distribution on 3 is up to more than 80%, digest and assimilate in process infant, probably can form calcium salt or the magnesium salts of water-fast saturated lipid acid, impact fat and the absorption of mineral substance, cause the specific absorption of fat and mineral substance by low, easy generation constipation or the illness such as dry and hard.
Although breast milk is the optimum food of baby, due to a variety of causes, worldwide the supply of breast milk is difficult to the needs meeting infant physical growth.Thus, the research and development of breast milk fat substitutes and production problem are badly in need of solving.Breast milk fat substitutes, refers to the Structure grease with human milk fat similar structures and function of synthetic, is generally 1,3-bis-oleic acid-2-palmitinic acid triglyceride (OPO).At present; adopt the method for lipase-catalyzed synthesis; namely with on glycerol backbone Sn-2 position containing enriching the triglyceride level of palmitinic acid or monoglyceride for raw material; with acry radical donor (free lipid acid), the building-up reactions that transesterify occurs is the main method of producing breast milk fat substitutes at present.Use the triglyceride level that the method is obtained, close not only with natural human dairy fats on the total fatty acids composition of glyceryl ester, and the distribution situation of these lipid acid on the glycerol backbone of triglyceride level also meets the situation of natural human milk fat.Loders Croklaan company of Holland reacts with oleic acid continuous acidolysis the breast milk fat substitutes produced with Lipozyme RM IM catalysis palm stearin (PPP) and ratifies for commercially producing and obtaining China's new resource food.The people such as Nese produce human milk substitute with the polyunsaturated fatty acid (DHA, EPA) of Lipozyme RM IM catalysis hazelnut oil lipid acid after urea enrichment with Trihexanoylglycerol acidolysis reaction.And adopt response phase method optimization to obtain optimum experiment condition to be: temperature of reaction 55 DEG C, substrate is than being 12.4:1 (mol ratio), reaction times 24h.The palmitinic acid massfraction producing sn-2 position reaches the human milk substitute of 76.6%.The sn-1 such as Yang Tiankui, 3 specific lipase Lipozyme IM catalysis free fatty acidies and lard acidolysis reaction are prepared lipid acid and are formed the human milk substitute substantially meeting people's butterfat and form.After response phase method optimization, obtain optimal conditions is: moisture content 3.7% (in enzyme amount), temperature of reaction 61 DEG C, the mol ratio 2.4:1 of lipid acid and lard.The people such as Schmid react with first catalysis palm stearin (PPP) of specific lipase and ethanolysis and produce Sn-2 mono-glycerides, and mono-glycerides generates highly purified OPO type human milk substitute again under the effect of 1,3-specific lipase with oleic acid esterification.In product OPO, Sn-2 position palmitic acid content reaches 96%, Sn-1, and 3-position oleic acid occupation rate reaches 90%.But because this process employs highly purified triglyceride as raw material, cost intensive, industrialized possibility is little.Namely people's butterfat of Unilever company is produced is use plam oil and palm-kernel oil 1, again ester exchange offspring and the sunflower seed oil of high gas oil ratio content, the rapeseed oil of high linoleic acid content and Oleum Cocois are allocated by a certain percentage after carrying out transesterify under 3 selected fat enzyme catalysiss, in the triglyceride mixture obtained, saturated fatty acid accounts for 30%, and the saturated fatty acid wherein on sn-2 position accounts for 40% of total saturated fatty acid.The Lipozyme RM IM specific lipase catalysis tripalmitin and Oleum Cocois, safflower oil and soybean oil such as C.O.Maduko carry out transesterification reaction, and reaction product and goat butterfat obtain female emulsified fat product after allocating.
Prior art Problems existing in the process preparing OPO is: other palmitinic acid of technique many employings technical grade synthesis Trihexanoylglycerol, and then catalyzes and synthesizes with the grease of high-purity oleic acid or high gas oil ratio content.This raw materials technology source is unstable, and quality product is difficult to keep stable, (palmitinic acid market value is about 8000-9000 yuan/ton, and high-purity oleic acid is about 12000-15000 yuan/ton) on the high side.
Summary of the invention
The object of this invention is to provide a kind of method of raw materials enjoy stable sources, cheap OPO.The constant product quality obtained by the method, quality is superior.
Total technical conceive of the present invention is: plam oil is the oil (PalmOil) squeezed out from the palm fibre fruit pulp oil palm tree.Plam oil is mainly containing palmitinic acid (C16) and oleic acid (C18) two kinds of prevailing lipid acid, and palmitic degree of saturation is about 50%, and it is used more than the history of 5,000 years as whole food by people.In plam oil, glyceryl ester composition is main with 1,3-bis-palmitinic acid-2-oleic three ester (POP), has the structure contrary with breast milk, thus plam oil can not be directly used in allotment infant food.But, containing the two kinds of basic lipid acid produced required for OPO (OPO) in plam oil; Meanwhile, it is large that plam oil has output, the advantages such as price is low, stay in grade, resets, will become the optimum feed stock of producing breast milk fat substitutes if its structure can be carried out adjustment.
The technical scheme realizing the object of the invention is: raw material based on plam oil, oleic acid and palmitic acid mixture is prepared by hydrolysis plam oil, being separated again through palmitinic acid and oleic acid, and with the palmitinic acid after being separated for Material synthesis tripalmitin (PPP); React finally by lipase-catalyzed oleic acid and tripalmitin and produce OPO (OPO).
The concrete steps of technique scheme are as follows:
1. be raw material with plam oil, adopt chemical an acidic catalyst or lipase to be catalyzer, hydrolysis plam oil, obtained based on the fatty acid mixt of oleic acid and palmitinic acid, and Removal of catalyst.
2. the oleic acid that 1. obtains of separating step and palmitic acid mixture, obtain purer oleic acid and palmitinic acid.
3. the palmitinic acid 2. obtained with step, for raw material, adds glycerine, and with an acidic catalyst or lipase for catalyst synthesizes tripalmitin.Used catalyst is removed after reaction.
4. with the oleic acid of 3. the obtained tripalmitin of step and step 2. resulting separation for raw material, employing lipase is catalyzer, and synthesis has the OPO of ad hoc structure.Catalyzer lipase used is separated after reaction.
5. separating step 4. in remaining glyceryl ester and lipid acid, obtain finished product OPO, both breast milk fat substitutes.
Above-mentioned steps 1. in the plam oil that adopts comprise former palm fibre oil and fractionated palm oil carries all kinds of plam oil goods processed and obtain.
Above-mentioned steps 1. in acidic chemical catalyzer be liquid acid or all kinds of solid acid catalyst.Liquid acid comprises sulfuric acid, phosphoric acid, hydrochloric acid, Phenylsulfonic acid.
When above-mentioned steps 1. in the catalyzer that adopts be acidic chemical catalyzer time, reaction conditions is: reaction adds plam oil quality 3-20 water doubly, catalyst charge is 0.01% to 10% of plam oil quality, temperature of reaction is 30 DEG C-90 DEG C, when adopting high-pressure reactor, temperature of reaction can be 90 DEG C to 180 DEG C, and the reaction times is 2-24 hour.If when this acidic chemical catalyst agent is liquid acid, then adopt neutralization point phase method Removal of catalyst; If when acidic chemical catalyzer is solid acid, then adopts and filter or centrifugal method Removal of catalyst.
When above-mentioned steps 1. in the catalyzer that adopts be lipase time, reaction conditions is: reaction adds plam oil quality 8-40 water doubly, and catalyst charge is 0.1% to 30% of plam oil quality, and temperature of reaction is 30 DEG C-60 DEG C, and the reaction times is 8-48 hour.The separation of catalyzer adopts filters or centrifugally operated.
The above-mentioned steps 2. middle method being separated oleic acid and palmitinic acid can adopt crystallization process or rectification method.
Above-mentioned steps 3. in acidic chemical catalyzer be liquid acid or all kinds of solid acid catalyst, liquid acid comprises sulfuric acid, phosphoric acid, hydrochloric acid, Phenylsulfonic acid.
When above-mentioned steps 3. in catalyzer be acidic chemical catalyzer time, reaction conditions is: reaction adds palmitinic acid theoretical molar than 1-1.5 glycerine doubly, catalyst charge is 0.01% to 10% of plam oil quality, and temperature of reaction is 60 DEG C-180 DEG C, and the reaction times is 3-10 hour.If catalyzer is liquid acid, then adopt neutralization point phase method separating catalyst; If catalyzer is solid acid, then adopts and filter or centrifugal Removal of catalyst.
When above-mentioned steps 3. in catalyzer be lipase time, reaction conditions is: reaction adds palmitinic acid theoretical molar than 1-1.5 glycerine doubly, catalyst charge is 0.1% to 30% of plam oil quality, and temperature of reaction is 30 DEG C-60 DEG C, and the reaction times is 10-48 hour.Adopt and filter or centrifugal Removal of catalyst.
Above-mentioned steps 4. in the lipase that adopts comprise various commercial lipase as Novozyme435 (Novozymes Company's commercialization lipase), Lipozyme TL-IM (Novozymes Company's commercialization lipase), Lipozyme RM-IM (Novozymes Company's commercialization lipase), the immobilized lipases such as Candida sp.99-125 lipase (production of Beijing Kai Tai new millennium company limited), and each yeast-like fungi, fungi, the lipase that bacterium and engineering bacteria fermentation are produced.Step reaction conditions is 4.: tripalmitin and oleic acid mass ratio are 1:1 to 1:6, lipase add-on is the 1%-30% of tripalmitin quality, temperature of reaction is 30 DEG C-60 DEG C, reaction can add the water of tripalmitin quality 0.1%-5%, and the reaction times is 6-48 hour.The separation of lipase adopts centrifugal or filter operation.
Above-mentioned steps 5. in lock out operation can select crystallization, rectifying, evaporation or solvent extraction.
The present invention has positive effect: the method produces the lipid acid needed for OPO by the preparation of hydrolysis plam oil, catalyze and synthesize in employing and locate the polystep reactions such as Enzyme catalyzed synthesis, palmitinic acid is converted into the basic material OPO (OPO) of baby's video.Due to the principal articles of export that plam oil is Southeast Asian countries, there is steady sources, the advantage such as quality controllable.Meanwhile, in recent years plam oil in the international market price tend towards stability, and far below other kinds natural fats and oils always.The advantages such as thus the method has raw materials enjoy stable sources, cheap, constant product quality, and quality is superior.
Embodiment
(embodiment 1)
The present embodiment has following steps:
1. select Candida sp.99-125 lipase to be hydrolysis reaction catalyzer so that commercially available former palm fibre is oily for raw material, reaction adds the former palm fibre oil of 1kg, 20kg water and 100g lipase.45 DEG C are reacted 48 hours, and former brown oleic acid valency is increased to 189mgKOH/g by initial 5.6mgKOH/g.Filtering separation lipase.
2. the separation oleic acid adopting the method for crystallization separation separating step 1. to obtain and palmitinic acid, obtain thick oleic acid 220g, thick palmitinic acid 710g after separation.
3. adopt sulfuric acid as tripalmitin synthetic catalyst, add step and be 2. separated the thick palmitinic acid 700g obtained, add glycerine 90g, sulfuric acid 15g, temperature of reaction 90 DEG C, 3 hours reaction times.Na is adopted after reaction
2cO
3solution neutralisation of sulphuric acid, obtains the tripalmitin 750g of purity 92% after phase-splitting.
The tripalmitin of the 70g 4. 3. obtained with step is for raw material, add the thick oleic acid 220g that step is 2. obtained, with 10g Novozyme435 (Novozymes Company's commercialization lipase) for catalyzer, 40 DEG C are reacted 24 hours, filtering separation lipase after reaction.
5. at 250 DEG C, the lipid acid under 100Pa condition in vacuum-evaporation step reaction solution 4., obtains product 68g, and analyze through HPLC-MS, in product, OPO content is 52%, and indices meets relevant national standard.
(embodiment 2)
The present embodiment has following steps:
1. with commercially available 44 degree of plam oils for raw material, select sulfuric acid to be hydrolysis reaction catalyzer, reaction add 1kg plam oil, 10kg water and 20g sulfuric acid.120 DEG C of compressive reactions 12 hours, plam oil acid value is increased to 176mgKOH/g by initial 3.2mgKOH/g.Neutralisation of sulphuric acid.
2. the oleic acid adopting the method for crystallization separation separating step 1. to obtain and palmitinic acid, obtain thick oleic acid 250g, thick palmitinic acid 690g after separation.
3. adopt sulfuric acid as tripalmitin synthetic catalyst, add step and be 2. separated the thick palmitinic acid 650g obtained, add glycerine 80g, sulfuric acid 15g, temperature of reaction 90 DEG C, 3 hours reaction times.Na is adopted after reaction
2cO
3solution neutralisation of sulphuric acid, obtains the tripalmitin 700g of purity 90% after phase-splitting.
The tripalmitin of the 70g 4. 3. obtained with step is for raw material, add the thick oleic acid 200g that step is 2. obtained, with 5g Candida sp.99-125 lipase (lipase from candida sp, Beijing Kai Tai new millennium company limited produces) be catalyzer, 45 DEG C are reacted 18 hours, filtering separation lipase after reaction.
5. lipid acid in the reaction solution be separated by the method for crystallization, obtains product 62g, and analyze through HPLC-MS, in product, OPO content is 48%, and indices meets relevant national standard.
(embodiment 3)
The present embodiment has following steps:
1. with Malaysian import edible palm oil for raw material, select Candida sp.99-125 lipase (lipase from candida sp, Beijing Kai Tai new millennium company limited produces) be hydrolysis reaction catalyzer, reaction adds 10kg plam oil, 100kg water and 1kg lipase.50 DEG C are reacted 48 hours, and plam oil acid value is increased to 179mgKOH/g by initial 0.6mgKOH/g.
2. the oleic acid adopting the method separating step of Crystallization Separation 1. to obtain and palmitinic acid, obtain thick oleic acid 2.8kg after separation, thick palmitinic acid 7.0kg.
3. adopt sulfuric acid as tripalmitin synthetic catalyst, add step and be 2. separated the thick palmitinic acid 7kg obtained, add glycerine 0.9kg, sulfuric acid 150g, temperature of reaction 110 DEG C, 3 hours reaction times.Na is adopted after reaction
2cO
3solution neutralisation of sulphuric acid, obtains the tripalmitin 7.4kg of purity 95% after phase-splitting.
The tripalmitin of the 1kg 4. 3. obtained with step is for raw material, add the thick oleic acid 2.5kg that step is 2. obtained, with 200g Candida sp.99-125 lipase (lipase from candida sp, Beijing Kai Tai new millennium company limited produces) be catalyzer, 45 DEG C are reacted 18 hours, filtering separation lipase after reaction.
5. under the condition of heating, vacuumize the lipid acid in evaporation reaction solution, obtain product 980g, analyze through HPLC-MS, in product, OPO content is 58%.
Each embodiment is the explanation to the specific embodiment of the present invention above; but not limitation of the present invention; those skilled in the art without departing from the spirit and scope of the present invention; can also make various conversion and obtain corresponding equivalent technical scheme, therefore all equivalent technical schemes all should be included into scope of patent protection of the present invention.
Claims (10)
1. the preparation method of 3-bis-oleic acid-2-palmitic acid three ester, it is characterized in that there are following steps: 1. raw material based on plam oil, under the catalysis of catalyzer, prepare oleic acid and palmitic acid mixture by hydrolysis plam oil, 2. palmitinic acid is separated with oleic acid mixture; 3. under catalyst action, tripalmitin is synthesized with the palmitinic acid after being separated for raw material; 4. reacted by lipase-catalyzed oleic acid and tripalmitin and produce OPO.
2. the preparation method of OPO according to claim 1, is characterized in that: also comprise step 5., separating step 4. in remaining glyceryl ester and lipid acid, obtain finished product OPO, both breast milk fat substitutes.
3. the preparation method of OPO according to claim 2, is characterized in that: step lock out operation is 5. crystallization, rectifying, evaporation or solvent extraction.
4., according to the preparation method of the OPO one of claims 1 to 3 Suo Shu, it is characterized in that: step 1. in the plam oil that adopts comprise former palm fibre oil and fractionated palm oil carries all kinds of plam oil goods processed and obtain.
5., according to the preparation method of the OPO one of claims 1 to 3 Suo Shu, it is characterized in that:
Step 1. in catalyzer be chemical an acidic catalyst or lipase; After being hydrolyzed, Removal of catalyst;
Step 3. in catalyzer be chemical an acidic catalyst or lipase; After being hydrolyzed, Removal of catalyst.
6. the preparation method of OPO according to claim 5, is characterized in that:
Step 1. in catalyzer be chemical an acidic catalyst, acidic chemical catalyzer is liquid acid or solid acid catalyst; Liquid acid comprises sulfuric acid, phosphoric acid, hydrochloric acid or Phenylsulfonic acid; Reaction conditions is: reaction adds plam oil quality 3-20 water doubly, catalyst charge is 0.01% to 10% of plam oil quality, and temperature of reaction is 30 DEG C-90 DEG C, when adopting high-pressure reactor, temperature of reaction can be 90 DEG C to 180 DEG C, and the reaction times is 2-24 hour; When acidic chemical catalyzer is liquid acid, adopt neutralization point phase method Removal of catalyst; When acidic chemical catalyzer is solid acid, adopts and filter or centrifugal method Removal of catalyst;
Step 3. in catalyzer be chemical an acidic catalyst, acidic chemical catalyzer is liquid acid or solid acid catalyst; Liquid acid comprises sulfuric acid, phosphoric acid, hydrochloric acid or Phenylsulfonic acid; Reaction conditions is: reaction adds palmitinic acid theoretical molar than 1-1.5 glycerine doubly, and catalyst charge is 0.01% to 10% of plam oil quality, and temperature of reaction is 60 DEG C-180 DEG C, and the reaction times is 3-10 hour; When acidic chemical catalyzer is liquid acid, adopt neutralization point phase method Removal of catalyst; When acidic chemical catalyzer is solid acid, adopts and filter or centrifugal method Removal of catalyst.
7. the preparation method of OPO according to claim 5, is characterized in that:
Step 1. in catalyzer be lipase, reaction conditions is: reaction adds plam oil quality 8-40 water doubly, and catalyst charge is 0.1% to 30% of plam oil quality, and temperature of reaction is 30 DEG C-60 DEG C, and the reaction times is 8-48 hour; The separation of catalyzer adopts filters or centrifugally operated;
Step 3. in catalyzer be lipase, reaction conditions is: reaction adds palmitinic acid theoretical molar than 1-1.5 glycerine doubly, and catalyst charge is 0.1% to 30% of plam oil quality, and temperature of reaction is 30 DEG C-60 DEG C, and the reaction times is 10-48 hour; Adopt and filter or centrifugal method separating catalyst.
8. according to the preparation method of the OPO one of claims 1 to 3 Suo Shu, it is characterized in that: the step 2. middle method being separated oleic acid and palmitinic acid is crystallization process or rectification method.
9. according to 1 one of claims 1 to 3 Suo Shu, the preparation method of 3-bis-oleic acid-2-palmitic acid three ester, is characterized in that: step 4. in the lipase that adopts be the lipase that immobilized lipase, each yeast-like fungi, fungi, bacterium and engineering bacteria fermentation are produced; Step reaction conditions is 4.: tripalmitin and oleic acid mass ratio are 1:1 to 1:6, lipase add-on is the 1%-30% of tripalmitin quality, temperature of reaction is 30 DEG C-60 DEG C, reaction can add the water of tripalmitin quality 0.1%-5%, and the reaction times is 6-48 hour; The separation of lipase adopts centrifugal or filter operation.
10. according to claim 91, the preparation method of 3-bis-oleic acid-2-palmitic acid three ester, it is characterized in that: Novozyme435 (Novozymes Company's commercialization lipase), Lipozyme TL-IM (Novozymes Company's commercialization lipase), Lipozyme RM-IM (Novozymes Company's commercialization lipase), Candida sp.99-125 lipase (production of Beijing Kai Tai new millennium company limited), and each yeast-like fungi, fungi, the lipase that bacterium and engineering bacteria fermentation are produced.
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| CN104996576A (en) * | 2015-08-28 | 2015-10-28 | 海普诺凯营养品有限公司 | Goat milk powder for infant and preparation method thereof |
| CN108841880A (en) * | 2018-08-01 | 2018-11-20 | 浙江汇能生物股份有限公司 | A kind of preparation method of 1,3-Dioleic acid-2-palmitoyl triglyceride |
| CN109275729A (en) * | 2018-11-12 | 2019-01-29 | 黑龙江飞鹤乳业有限公司 | A kind of preparation method for compounding grease and infant formula goat milk powder and the milk powder containing the compounding grease of simulation breast milk fatty acids |
| CN109566769A (en) * | 2018-11-15 | 2019-04-05 | 江南大学 | A kind of preparation method of the fat or oil composition rich in OPO and OPL |
| WO2020238010A1 (en) * | 2019-05-25 | 2020-12-03 | 华南理工大学 | Method for producing special oil opo using microbial fermentation |
| CN112195199A (en) * | 2020-10-29 | 2021-01-08 | 赞宇科技集团股份有限公司 | Production method of 1, 3-dioleoyl-2-palmitic acid triglyceride |
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| CN113584094A (en) * | 2021-07-30 | 2021-11-02 | 江南大学 | Preparation method of 1,3 unsaturated-2-saturated fatty acid structure triglyceride based on milk fat |
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| CN113943605A (en) * | 2021-09-27 | 2022-01-18 | 嘉必优生物技术（武汉）股份有限公司 | Method for winterization and fractionation of microbial oil |
| WO2022045953A1 (en) * | 2020-08-31 | 2022-03-03 | Aak Ab (Publ) | A process for production of a vegetable oil composition having at least 50% palmitic acid present in the sn2-position out of total palmitic acid in the triglycerides of the vegetable oil composition |
| CN114164048A (en) * | 2021-12-06 | 2022-03-11 | 润科生物工程（福建）有限公司 | Preparation method of high-content DHA grease |
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| CN104996576A (en) * | 2015-08-28 | 2015-10-28 | 海普诺凯营养品有限公司 | Goat milk powder for infant and preparation method thereof |
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